Andrea Chesleigh is the Chief Operating Officer and Chief Product Officer at Spresso, where she builds AI and SaaS solutions for ecommerce and enterprise clients. Over the past two decades, she has led product and digital strategy at companies like Verizon, Zappos, Rent the Runway, Boxed, and One Kings Lane, guiding teams through growth, complexity, and change.
She began her career in product and digital roles, drawn to the challenge of building systems that actually work for customers, teams, and the business. Over time, she leaned into the messy middle: where strategy meets execution, and where product intersects with ops, data, and finance. That path led her from product leadership into operational ownership. Today, she works across product, go-to-market, data science, and strategic finance, turning ambiguity into action and helping organizations scale with intention.
Outside of her day-to-day work, Andrea is deeply committed to mentorship and community. She co-led the NYC chapter of Women in Product and now serves on the Executive Edge Council. She has also been selected for fellowships with Primary Venture Partners and On Deck, where she supports founders and rising product leaders at the intersection of strategy, execution, and growth.
Andrea cares deeply about helping product leaders develop the mindset and skill set to lead at the executive level. Too often, leaders are asked to “act like execs” without being offered the tools or support to do it well. In recent years, she has started writing and sharing the frameworks she’s found most useful, practical ways to build clarity, lead with conviction, and navigate the emotional reality of leadership.
Whether she’s operating, writing, or speaking, Andrea’s goal is always the same: to help others lead with clarity, courage, and calm, even when things feel foggy, political, or high-stakes. For her, product leadership isn’t just about vision or roadmaps - it’s about making hard calls, holding the line when it’s unpopular, and still showing up with heart.
She began her career in product and digital roles, drawn to the challenge of building systems that actually work for customers, teams, and the business. Over time, she leaned into the messy middle: where strategy meets execution, and where product intersects with ops, data, and finance. That path led her from product leadership into operational ownership. Today, she works across product, go-to-market, data science, and strategic finance, turning ambiguity into action and helping organizations scale with intention.
Outside of her day-to-day work, Andrea is deeply committed to mentorship and community. She co-led the NYC chapter of Women in Product and now serves on the Executive Edge Council. She has also been selected for fellowships with Primary Venture Partners and On Deck, where she supports founders and rising product leaders at the intersection of strategy, execution, and growth.
Andrea cares deeply about helping product leaders develop the mindset and skill set to lead at the executive level. Too often, leaders are asked to “act like execs” without being offered the tools or support to do it well. In recent years, she has started writing and sharing the frameworks she’s found most useful, practical ways to build clarity, lead with conviction, and navigate the emotional reality of leadership.
Whether she’s operating, writing, or speaking, Andrea’s goal is always the same: to help others lead with clarity, courage, and calm, even when things feel foggy, political, or high-stakes. For her, product leadership isn’t just about vision or roadmaps - it’s about making hard calls, holding the line when it’s unpopular, and still showing up with heart.
